EP1180943B1 - Edible compositions containing trehalose - Google Patents
Edible compositions containing trehalose Download PDFInfo
- Publication number
- EP1180943B1 EP1180943B1 EP00931397A EP00931397A EP1180943B1 EP 1180943 B1 EP1180943 B1 EP 1180943B1 EP 00931397 A EP00931397 A EP 00931397A EP 00931397 A EP00931397 A EP 00931397A EP 1180943 B1 EP1180943 B1 EP 1180943B1
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- European Patent Office
- Prior art keywords
- solution
- edible composition
- composition according
- trehalose
- substances
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Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/30—Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/32—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds
- A23G1/40—Cocoa products, e.g. chocolate; Substitutes therefor characterised by the composition containing organic or inorganic compounds characterised by the carbohydrates used, e.g. polysaccharides
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/02—Apparatus specially adapted for manufacture or treatment of sweetmeats or confectionery; Accessories therefor
- A23G3/0236—Shaping of liquid, paste, powder; Manufacture of moulded articles, e.g. modelling, moulding, calendering
- A23G3/0252—Apparatus in which the material is shaped at least partially in a mould, in the hollows of a surface, a drum, an endless band, or by a drop-by-drop casting or dispensing of the material on a surface, e.g. injection moulding, transfer moulding
- A23G3/0289—Compression moulding of paste, e.g. in the form of a ball or rope or other preforms, or of a powder or granules
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G3/00—Sweetmeats; Confectionery; Marzipan; Coated or filled products
- A23G3/02—Apparatus specially adapted for manufacture or treatment of sweetmeats or confectionery; Accessories therefor
- A23G3/10—Candy-pulling machines ; Processes or apparatus for making cotton candy or candy floss
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/30—Artificial sweetening agents
- A23L27/33—Artificial sweetening agents containing sugars or derivatives
Definitions
- the present invention relates to edible compositions containing amorphous solid trehalose.
- the present invention also relates to methods of manufacture of compositions containing amorphous solid trehalose.
- sugar alcohols such as mannitol, sorbitol, xylitol, maltitol, isomalt, lactitol and erythritol as non-cariogenic sweeteners in products such as boiled sweets, candy, chocolate and chewing gum. It is also known to use the sugar alcohols as excipients in the manufacture of medicaments for oral administration such as compressed tablets and lozenges to be sucked or chewed in the mouth.
- sweeteners possess strongly endothermic heats of solution in the crystalline state, ranging typically from -39 kJ/kg for isomalt to -111 kJ/kg for sorbitol and -185 kJ/kg for crystalline erythritol (values are taken from the LFRA Ingredients Handbook - Sweeteners, J.M. Dalzell Ed., December 1996).
- Some sugars are also known to have strongly negative heats of solution. For example, dextrose monohydrate has a heat of solution of -105 kJ/kg.
- Edible products or pharmaceuticals for oral administration containing ingredients with strongly negative heats of solution can give rise to a noticeable cooling in the mouth when the products are consumed.
- This cooling sensation is quite acceptable when the product contains menthol flavours such as mint, but it is undesirable when the product is non-menthol flavoured or the product is, for example, chocolate.
- Trehalose is a naturally occurring non-reducing disaccharide. Specifically, trehalose is ⁇ -D-glucopyranosyl- ⁇ -D-glucopyranoside. It is present in certain drought-resistant plants such as Selaginella lepidophylla, and can also be prepared by fermentation. One suitable fermentation process is described in EP-A-0693558.
- GB-A-2206273 and GB-A-2187191 describe the use of trehalose as an additive to stabilize proteins and foodstuffs against degradation upon drying.
- JP-A-60319503 describes the use of trehalose as a cryoproctectant for freeze-dried food. Up to 70% of trehalose on a dry weight basis is added to the food before freeze drying.
- EP-A-0622025 describes the use of crystalline trehalose for the formulation of food products having reduced cariogenicity and calorie content compared to sucrose-containing sweeteners.
- JP-A-92038642 describes confectionery compositions having low cariogenicity comprising trehalose and a sugar alcohol selected from erythritol, xylitol, mannitol, sorbitol, xylobiotol, maltitol and lactitol. These compositions apparently contain crystalline trehalose, probably trehalose dihydrate.
- Crystalline trehalose dihydrate of the kind commercially available up until now has been measured by the present inventors to have a heat of solution of -52 kJ/kg.
- the present inventors have also found, surprisingly, that the heat of solution of amorphous trehalose formed by spray drying or melt spinning is actually positive, in the range 66-70 kJ/kg.
- the present invention provides an edible composition comprising at least 10% on a dry weight basis of one or more substances having an endothermic heat of solution of at least -30kJ/kg and at least 10% on a dry weight basis of amorphous solid trehalose.
- substance having an endothermic heat of solution refers to food- or pharmaceutically-acceptable substances that are soluble in water under physiological conditions and have an endothermic heat of solution of at least (i.e. at least as endothermic as) -30kJ/kg
- the substances having an endothermic heat of solution may for example be selected from the group consisting of soluble pharmaceuticals, pharmaceutically acceptable excipients, foodstuffs, flavorings, dietary supplements, or mixtures of such substances having negative heats of solution.
- at least one of the substances having an endothermic heat of solution is a sweetener.
- the substances may comprise dextrose monohydrate or even crystalline trehalose dihydrate.
- the susbstances comprises a sugar alcohol.
- sugar alcohol refers to a hydrogenation product of a sugar. During hydrogenation, the aldehyde or ketone groups of the sugars are reduced to hydroxy groups.
- the sugar alcohol is selected from the group consisting of mannitol, sorbitol, xylitol, maltitol, isomalt, lactitol, erythritol, and mixtures thereof.
- At least one of the substances having an endothermic heat of solution is substantially crystalline.
- the substances having an endothermic heat of solution are soluble in water at 25°C to the extent of at least 25 g/liter, more preferably at least 100 g/liter.
- at least one of the substances having an endothermic heat of solution is substantially anhydrous in the products according to the invention except for water of crystallisation, if any.
- the one or more substances having an endothermic heat of solution exhibit a heat of solution equal to or more endothermic than -30 kJ/kg, more preferably more endothermic than -50 kJ/kg, and most preferably more endothermic than -70 kJ/kg.
- the edible composition according to the present invention comprises at least 20% by weight, of the substances having heats of solution equal to or more endothermic than -30 kJ/kg.
- the edible composition according to the present invention comprises at least 20% by weight of amorphous trehalose.
- the edible compositions may, of course, comprise other edible or pharmaceutical components that do not contribute substantially to the heat of solution.
- the solid trehalose is substantially amorphous. That is to say, it is characterized by a diffuse X-ray diffraction pattern, as shown in Fig. 2.
- Amorphous trehalose can also be distinguished from crystalline trehalose by differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), solid state nuclear magnetic resonance spectroscopy (NMR), microscopic techniques and other techniques.
- DSC differential scanning calorimetry
- FTIR Fourier transform infrared spectroscopy
- NMR solid state nuclear magnetic resonance spectroscopy
- Amorphous solid trehalose can be made by freeze-drying, spray drying, vacuum drying or oven drying aqueous solutions of trehalose.
- Amorphous trehalose can also be formed by melt spinning of solid trehalose in a candy floss-type machine.
- the substantially amorphous solid trehalose has a heat of solution in water at 25°C of at least 30 kJ/kg, more preferably at least 60 kJ/kg. The latter value corresponds to substantially amorphous and anhydrous trehalose.
- the edible composition comprises less than 20% by weight of water, more preferably less than 10% by weight of water, and still more preferably less than 5% by weight of water. Higher water contents would cause the amorphous trehalose to revert to a crystalline form, or even to dissolve thereby making the heat of solution irrelevant to the sensation of the composition in a consumer's mouth.
- the weight ratio of the substance having an endothermic heat of solution to substantially amorphous solid trehalose is selected to modify the sensation of heating or cooling in the mouth when the edible composition is consumed.
- the weight ratio of substance having an endothermic heat of solution to trehalose is preferably in the range of 1:10 to 3:1, more preferably from 1:4 to 1:1.
- the ratio of substance having an endothermic heat of solution to trehalose is selected such that the heat of solution of the edible composition is greater than (i.e. less endothermic than) -50 kJ/kg, more preferably greater than -30 kJ/kg, still more preferably greater than -15 kJ/kg, and most preferably greater than -5 kJ/kg.
- the present invention is especially suitable for edible compositions in which the substances having an endothermic heat of solution and the trehalose together make up a substantial fraction of the composition. Preferably, they together make up at least 25%, more preferably at least 50% and still more preferably at least 75%; at least 90% or at least 95% by weight of the composition.
- the composition consists essentially of sugar alcohols and/or sugars having an endothermic heat of solution and the amorphous trehaiose, for example when the composition is a sweetener composition. More preferably, the sweetener composition is a free-flowing, particulate sweetener composition.
- compositions include chocolate, compressed tablets and hard sweets that are sucked in the mouth, and chewing gum.
- the edible compositions of this invention may form part of a larger foodstuff, for example the compositions may be present as a coating on an edible core.
- the edible compositions according to the present invention are also less calorific and less cariogenic than compositions having equivalent organoleptic properties made with conventional sugars such as sucrose.
- the present invention provides a method of manufacturing an edible composition comprising the step of dry mixing amorphous trehalose particles in an amount of at least 10% based on the dry weight of the composition with one or more other edible ingredients to form a dry mixture.
- the amorphous trehalose as hereinbefore defined is dry mixed in an amount of at least 20% by weight, more preferably at least 30% by weight based on the dry weight of the composition.
- dry mixing refers to mixing the particles substantially in the absence of water, preferably in the presence of less than 20% by weight of water, more preferably less than 10% by weight of water and most preferably less than 5% by weight of water.
- the water content does not exceed these levels at any stage in the process after addition of the dry mixing step. This contrasts with the prior use of trehalose as a cryoprotectant in foodstuffs, where the trehalose is mixed with the aqueous foodstuff prior to freeze drying.
- the particle size of the trehalose used in the methods of this invention is less than 1mm, preferably less than 0.1mm, in order to achieve the desired intimate mixing.
- the dry mixture preferably undergoes further processing steps, such as compressing the dry mixture to form a tablet, or forming the mixture into a coating.
- the mixture further comprises a fat
- the method further comprises melting the fat in the dry mixture to form a fluid dry mixture, such as melted chocolate.
- the dry mixture has substantially the same composition as the edible composition produced by the process.
- the processes according to the present invention can be used to make compositions according to the present invention as hereinbefore described.
- the processes can also be used to make edible compositions containing little or no substances having endothermic heats of solution, in which case the edible compositions containing amorphous trehalose have a net exothermic heat of solution that gives the compositions a warming effect in the mouth when they are consumed.
- the dry mixture in the process according to the present invention has an exothermic heat of solution in water at 25°C of at least +15kJ/kg, more preferably at least +30kJ/kg.
- the edible composition is selected from the group consisting of chocolate, compressed tablets, hard sweets that are sucked in the mouth, and chewing gum.
- Amorphous trehalose was prepared by the following methods:-
- Trehalose dihydrate supplied by Hayashibara Company and thought to have been manufactured in accordance with the method of EP-A-0693558 was dissolved in demineralised water to give a 40% trehalose solution at 40°C.
- the solution was spray dried using a Niro Minor spray drier at an inlet temperature of 21.5°C and an outlet temperature of 115°C.
- the moisture content of the product was 2% as measured by Karl-Fisher titration.
- Figure 1 shows a DSC thermogram of the spray-dried trehalose.
- Figure 2 shows X-ray diffractograms of powdered, crystalline trehalose dihydrate (for comparison) and the spray-dried trehalose. The diffuse diffractogram confirms that the spray-dried trehalose is substantially in the glassy state.
- Trehalose dihydrate was dissolved in demineralised water to give a 20% trehalose solution.
- the solution was frozen to -40°C, then freeze dried in an Edwards freeze dryer.
- a powdered material typical of freeze dried powder was obtained. The material was confirmed to be completely amorphous by DSC and X-ray powder diffraction.
- the spray dried trehalose obtained in procedure (a) was spun at high temperature using a candy floss type machine (Tornado Floss Machine) and filaments of glassy trehalose were obtained.
- Crystalline trehalose dihydrate was heated with a minimal amount of water on a hot plate for a few minutes until an isotropic melt was obtained. The melt was then rapidly cooled to room temperature to produce a clear glass.
- Glassy trehalose was prepared by vacuum drying trehalose dihydrate at 65°C for 96 hours.
- Glassy trehalose was prepared by heating trehalose dihydrate to 240°C in an oven.
- Edible sugar compositions according to the present invention were prepared by mixing spray dried trehalose prepared by Procedure 1(a) above with anhydrous crystalline xylitol (supplied by Xyrofin) in the following proportions.
- the temperature changes of a 4.8% solution (based on dry substance) were recorded upon dissolution: % Spray Dried Trehalose Temperature Changes (°C) 0 -1.7 25% -1.0 50% -0.4 75% +0.3 100% +0.8
- An edible sugar composition consisting essentially of crystalline erythritol and amorphous trehalose was prepared as follows.
- Spray dried trehalose prepared by Procedure 1(a) was blended with anhydrous crystalline erythritol (supplied by Cerestar) and the temperature changes of a 4.8% solution (based on dry substance) were recorded upon dissolution:- % Spray Dried Trehalose Temperate Changes (°C) 0 -2.1 25% -1.4 50% -0.7 75% +0.1 100% +0.8
- An edible candy floss composition was prepared by spinning a mixture of crystalline xylitol (30% by weight) and spray dried trehalose from procedure (a) above (70% by weight) in a Tornado Floss Machine.
- the candy floss was dissolved in an amount of 4.8% in water based on dry substance, and a temperature increase of 0.4°C was recorded.
- Compressed tablets in accordance with the present invention was prepared by thoroughly mixing the following ingredients using a Ploughshare mixer, followed by compressing the mixtures into 13mm diameter tablets using a Manesty F3 single punch tablet machine:- Ingredient Control Sample 1 Sample 2 Sorbitol 99.0 59.4 19.7 Amorphous Trehalose 0.00 39.6 78.8 Magnesium Stearate 1.0 1.0 1.0 Silicon Dioxide 0 0 0
- a chocolate having an exothermic heat of solution was prepared by a process in accordance with the present invention as described in Example 5.
- the composition was as follows: amorphous trehalose 47.0%, full cream milk powder 20.5%, cocoa mass 12.5%, cocoa butter 17.5%, butter oil 2.0%, lecithin (TOPCITHIN 200) 0.50% and vanillin crystals 0.30%.
- the process steps were as described in Example 4.
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- Molecular Biology (AREA)
- Inorganic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Nutrition Science (AREA)
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Abstract
Description
% Spray Dried Trehalose | Temperature Changes (°C) |
0 | -1.7 |
25% | -1.0 |
50% | -0.4 |
75% | +0.3 |
100% | +0.8 |
% Spray Dried Trehalose | Temperate Changes (°C) |
0 | -2.1 |
25% | -1.4 |
50% | -0.7 |
75% | +0.1 |
100% | +0.8 |
Ingredient | Control | Sample 1 | |
Crystalline Xylitol | 46.99 | 27.99 | 14.00 |
Amorphous Trehalose | 0.00 | 18.99 | 32.99 |
Full Cream Milk Powder | 20.49 | 20.49 | 20.49 |
Cocoa Mass | 12.50 | 12.50 | 12.50 |
Cocoa Butter | 17.50 | 17.50 | 17.50 |
Butter Oil | 2.00 | 2.00 | 2.00 |
Lecithin (Topcithin 200) | 0.50 | 0.50 | 0.50 |
Vanillin Crystals | 0.30 | 0.30 | 0.30 |
100% | 100% | 100% |
Six volunteers were asked to taste the three samples of chocolate and to score numerically any cooling effect in the mouth (not cooling at all = 0, very cooling = 5).
Ingredient | Control | Sample 1 | |
Sorbitol | 99.0 | 59.4 | 19.7 |
Amorphous Trehalose | 0.00 | 39.6 | 78.8 |
Magnesium Stearate | 1.0 | 1.0 | 1.0 |
Silicon Dioxide | 0 | 0 | 0 |
Claims (33)
- An edible composition comprising: at least 10% on a dry weight basis of one or more substances soluble in water at 25°C to the extent of at least 25 g/liter.and having an endothermic heat of solution of at least -30kJ/kg when measured at 25ºC; and at least 10% on a dry weight basis of amorphous solid trehalose.
- An edible composition according to claim 1, wherein one or more of said substances having an endothermic heat of solution is substantially crystalline.
- An edible composition according to any preceding claim, wherein one or more of said substances having an endothermic heat of solution is substantially anhydrous except for water of crystallisation.
- An edible composition according to any preceding claim, wherein one or more of said substances having an endothermic heat of solution is soluble in water at 25°C to the extent of at least 100 g/liter.
- An edible composition according to any preceding claim, wherein one or more of said substances having an endothermic heat of solution is a soluble pharmaceutical, a pharmaceutically acceptable excipient, a foodstuff, a flavoring, or a dietary supplement.
- An edible composition according to any preceding claim, wherein one or more of said substances having an endothermic heat of solution is a sweetener.
- An edible composition according to any preceding claim, wherein one or more of said substances having an endothermic heat of solution is selected from the group consisting of crystalline dextrose monohydrate, crystalline trehalose dihydrate and crystalline sugar alcohols.
- An edible composition according to claim 7 wherein the said one or more substances is selected from the group consisting of mannitol, sorbitol, xylitol, maltitol, isomalt, lactitol, and erythritol.
- An edible composition according to any preceding claim, wherein one or more of the said substances having an endothermic heat of solution has a heat of solution in water when measured at 25ºC more endothermic than -50 kJ/kg.
- An edible composition according to any preceding claim, wherein one or more of the said substances having an endothermic heat of solution has a heat of solution in water when measured at 25ºC more endothermic than -70 kJ/kg.
- An edible composition according to any preceding claim that comprises at least 20% by weight of one or more substances having a heat of solution in water when measured at 25ºC more endothermic than -30kJ/kg.
- An edible composition according to any preceding claim, wherein the substantially amorphous solid trehalose has a heat of solution in water when measured at 25ºC of at least +30 kJ/kg.
- An edible composition according to any preceding claim, wherein the substantially amorphous solid trehalose has a heat of solution in water when measured at 25ºC at least 60 kJ/kg.
- An edible composition according to any preceding claim, wherein the edible composition comprises less than 20% by weight of water.
- An edible composition according to claim 14 wherein the edible composition comprises less than 10% by weight of water.
- An edible composition according to claim 15 wherein the edible composition comprises less than 5% by weight of water.
- An edible composition according to any preceding claim, wherein, the weight ratio of the said one or more substances having an endothermic heat of solution to trehalose is in the range of 1:10 to 3:1.
- An edible composition according to any preceding claim, wherein, the weight ratio of the said one or more substances having an endothermic heat of solution to trehalose is in the range of from 1:4 to 1:1.
- An edible composition according to any preceding claim, wherein the ratio of the said substances having an endothermic heat of solution to trehalose is selected such that the heat of solution of the composition when measured at 25ºC is greater than (i.e. less endothermic than) -50 kJ/kg.
- An edible composition according to claim 20, wherein the ratio of the said substances having an endothermic heat of solution to trehalose is selected such that the heat of solution of the composition when measured at 25ºC is greater than (i.e. less endothermic than) -30 kJ/kg.
- An edible composition according to any preceding claim that comprises at least 20% by weight of the said amorphous trehalose, calculated on a dry weight basis.
- An edible composition according to any preceding claim in which the one or more substances having an endothermic heat of solution and the amorphous trehalose together make up at least 25% by weight of the composition, calculated on a dry weight basis.
- An edible composition according to claim 23 in which the one or more substances having an endothermic heat of solution and the amorphous trehalose together make up at least 50% by weight of the composition, calculated on a dry weight basis.
- An edible composition according to claim 23 in which the one or more substances having an endothermic heat of solution and the amorphous trehalose together make up at least 75% by weight of the composition, calculated on a dry weight basis.
- An edible composition according to claim 24 in which the one or more substances having an endothermic heat of solution and the amorphous trehalose together make up at least 90% by weight of the composition, calculated on a dry weight basis.
- An edible composition according to any preceding claim that consists essentially of sugar alcohols and/or sugars having an endothermic heat of solution and the amorphous trehalose
- An edible composition according to claim 26 that is a free-flowing, particulate sweetener composition.
- An edible composition according to any one of claims 1 to 25, which is a selected from the group consisting of chocolate, compressed tablets and hard sweets that are sucked in the mouth, and chewing gum.
- A method of manufacturing an edible composition according to any one of claims 1 to 28, comprising the step of dry mixing amorphous trehalose particles in an amount of at least 10% based on the dry weight of the composition with one or more other edible ingredients soluble in water at 25°C to the extent of at least 25 g/liter, and having an endothermic heat of solution of at least -30kJ/kg when measured at 25ºC, to form a dry mixture.
- A method according to claim 29, further comprising the step of compressing the dry mixture to form a tablet.
- A method according to claim 29, wherein the mixture further comprises a fat, and the method further comprises melting the fat in the dry mixture to form a fluid dry mixture.
- A method according to claim 29 wherein the dry mixture has an exothermic heat of solution in water when measured at 25°C of at least +15kJ/kg.
- A method according to claim 29 wherein the edible composition is selected from the group consisting of chocolate, compressed tablets, hard sweets that are sucked in the mouth, and chewing gum.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9911783A GB2350046B (en) | 1999-05-20 | 1999-05-20 | Edible compositions containing trehalose |
GB9911783 | 1999-05-20 | ||
PCT/GB2000/001914 WO2000070966A1 (en) | 1999-05-20 | 2000-05-18 | Edible compositions containing trehalose |
Publications (2)
Publication Number | Publication Date |
---|---|
EP1180943A1 EP1180943A1 (en) | 2002-02-27 |
EP1180943B1 true EP1180943B1 (en) | 2003-10-29 |
Family
ID=10853848
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP00931397A Expired - Lifetime EP1180943B1 (en) | 1999-05-20 | 2000-05-18 | Edible compositions containing trehalose |
Country Status (7)
Country | Link |
---|---|
US (1) | US6620791B1 (en) |
EP (1) | EP1180943B1 (en) |
AT (1) | ATE252850T1 (en) |
AU (1) | AU4935300A (en) |
DE (1) | DE60006230D1 (en) |
GB (1) | GB2350046B (en) |
WO (1) | WO2000070966A1 (en) |
Families Citing this family (23)
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GB2353933A (en) * | 1999-09-09 | 2001-03-14 | British Sugar Plc | Compositions comprising trehalose for forming tablets |
US7122376B2 (en) * | 2001-11-01 | 2006-10-17 | Facet Analytical Services And Technology, Llc | Calibration standards, methods, and kits for water determination |
US7049146B2 (en) | 2000-11-14 | 2006-05-23 | Facet Analytical Services And Technology, Llc | Calibration standards, methods, and kits for water determination |
AU2003270727A1 (en) * | 2002-09-17 | 2004-04-08 | Luna Innovations, Inc. | Remote temperature sensing of small volume and related apparatus thereof |
US7250548B2 (en) * | 2003-06-16 | 2007-07-31 | Kimberly-Clark Worldwide, Inc. | Absorbent article with temperature change member disposed on the outer cover and between absorbent assembly portions |
US20040254549A1 (en) * | 2003-06-16 | 2004-12-16 | Kimberly-Clark Worldwide, Inc. | Personal wear article with wetness indicator |
EP1500335A1 (en) * | 2003-07-23 | 2005-01-26 | Cerestar Holding Bv | Trehalose containing comestibles for sustained carboydrate energy release and reduced glycemic/insulinemic responses |
US20060188627A1 (en) * | 2003-07-23 | 2006-08-24 | Brouns Fredericus Johannes P H | Isomaltulose or trehalose containing comestibles for sustained carbohydrate energy release and increased fat oxidation |
US20060142716A1 (en) * | 2004-12-29 | 2006-06-29 | Kimberly-Clark Worldwide, Inc. | Absorbent article featuring a non-abrasive temperature change member |
US8129582B2 (en) * | 2004-12-29 | 2012-03-06 | Kimberly-Clark Worldwide, Inc. | Absorbent article featuring a temperature change member |
US20050196517A1 (en) * | 2005-02-14 | 2005-09-08 | Mars, Incorporated | Edible product having discrete regions with different heats of solution |
US7632978B2 (en) * | 2005-04-29 | 2009-12-15 | Kimberly-Clark Worldwide, Inc. | Absorbent article featuring an endothermic temperature change member |
FR2894435B1 (en) * | 2005-12-14 | 2010-09-03 | Roquette Freres | SUGAR-FREE CONFECTIONERY COMPRISING XYLITOL WITHOUT REFRESHING EFFECT |
AU2007281184A1 (en) * | 2006-07-31 | 2008-02-07 | Wm. Wrigley Jr. Company | Chewing gum products |
WO2008100853A1 (en) * | 2007-02-12 | 2008-08-21 | Wm. Wrigley Jr. Company | Confectionery products comprising polyols |
AU2008216453B2 (en) * | 2007-02-12 | 2011-07-28 | Wm. Wrigley Jr. Company | Coated confectionery products |
RU2581221C2 (en) | 2010-12-30 | 2016-04-20 | Вм. Ригли Дж. Компани | Hard candy composition (versions) |
WO2013106363A2 (en) | 2012-01-09 | 2013-07-18 | Wm. Wrigley Jr. Company | Gelled confection with reduced sugar |
JP6195848B2 (en) | 2012-01-27 | 2017-09-13 | ザ、リージェンツ、オブ、ザ、ユニバーシティ、オブ、カリフォルニアThe Regents Of The University Of California | Stabilization of biomolecules using sugar polymers |
MX2019000219A (en) | 2016-07-05 | 2019-09-04 | Glaxosmithkline Consumer Healthcare Holdings Us Llc | Oral dosage form containing a fast release exterior coating. |
CN106723059B (en) * | 2017-02-10 | 2020-07-10 | 苏州工业园区尚融科技有限公司 | Low-calorie health sugar and preparation method thereof |
JP2021036837A (en) * | 2019-09-05 | 2021-03-11 | 日新化工株式会社 | Chocolate and chocolate-coated food product |
JP7428270B2 (en) * | 2021-09-29 | 2024-02-06 | 不二製油株式会社 | Oil-based foods containing heat-generating materials |
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GB2187191B (en) | 1984-01-30 | 1989-11-01 | Quadrant Bioresources Ltd | Protection of proteins and the like |
GB8715238D0 (en) * | 1987-06-29 | 1987-08-05 | Quadrant Bioresources Ltd | Food process |
NZ246865A (en) * | 1992-01-22 | 1996-10-28 | Novo Nordisk As | Activated factor xiii (plasma transglutaminase) and its use in food products and compositions |
JPH05207223A (en) | 1992-01-28 | 1993-08-13 | Kanegafuchi Chem Ind Co Ltd | Check method for image sensor |
JP3168550B2 (en) * | 1992-12-02 | 2001-05-21 | 株式会社林原生物化学研究所 | Dehydrating agent, method for dehydrating hydrated material using the same, and dehydrated article obtained by the method |
EP0622025A3 (en) | 1993-04-28 | 1995-01-11 | Ajinomoto Kk | Sweet ice stuffs and jellied foods. |
JPH06319503A (en) * | 1993-05-17 | 1994-11-22 | Asahi Chem Ind Co Ltd | Novel freeze-dried food |
IL114030A (en) | 1994-06-27 | 2000-08-13 | Hayashibara Biochem Lab | Saccharide composition with a lesser reducibility its preparation and compositions containing it |
DE69529026T2 (en) | 1994-07-19 | 2003-07-17 | Hayashibara Biochem Lab | Trehalose, its production and its use |
JP3469694B2 (en) * | 1995-10-13 | 2003-11-25 | 長谷川香料株式会社 | Method for producing powdered fragrance |
JPH09163943A (en) * | 1995-12-15 | 1997-06-24 | Ajinomoto Co Inc | Cooked rice food for chilled distribution |
US5762961A (en) * | 1996-02-09 | 1998-06-09 | Quadrant Holdings Cambridge Ltd. | Rapidly soluble oral solid dosage forms, methods of making same, and compositions thereof |
JPH11140094A (en) * | 1997-10-31 | 1999-05-25 | Nippon Shokuhin Kako Co Ltd | Production of powdery trehalose |
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- 2000-05-18 WO PCT/GB2000/001914 patent/WO2000070966A1/en active Search and Examination
- 2000-05-18 EP EP00931397A patent/EP1180943B1/en not_active Expired - Lifetime
- 2000-05-18 AU AU49353/00A patent/AU4935300A/en not_active Abandoned
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DE60006230D1 (en) | 2003-12-04 |
EP1180943A1 (en) | 2002-02-27 |
GB2350046B (en) | 2002-12-18 |
GB2350046A (en) | 2000-11-22 |
AU4935300A (en) | 2000-12-12 |
GB9911783D0 (en) | 1999-07-21 |
WO2000070966A1 (en) | 2000-11-30 |
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